A selective de-O-methylation of guaiacyl lignans to corresponding catechol derivatives by 2-iodoxybenzoic acid (IBX). The role of the catechol moiety on the toxicity of lignans

Roberta Bernini, Maurizio Barontini, Pasquale Mosesso, Gaetano Pepe, Stefan M. Willför, Rainer E. Sjöholm, Patrik Christoffer Eklund, Raffaele Saladino

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    We report here the first selective de-O-methylation of a large panel of guaiacyl lignans to the corresponding catechol derivatives by using IBX as primary oxidant under green conditions (dimethyl carbonate-H(2)O solvent) through an in situ reduction procedure. The influence of the catechol moiety on the cytotoxicity and genotoxicity of new lignan derivatives has been investigated. The results obtained indicated that the presence of the catechol moiety sharply enhances the clastogenic potential (e. g. induction of chromosomal aberrations), the cytotoxicity and the modulation of cell cycle progression with respect to the parent compounds. Thus, despite the in vitro antioxidant activity usually described for catechol derivatives, our results show for the first time the generation of a clastogenic potential, highly indicative of a long-term genetic and cancer risk.
    Original languageUndefined/Unknown
    Pages (from-to)2367–2377
    Number of pages11
    JournalOrganic and Biomolecular Chemistry
    Issue number11
    Publication statusPublished - 2009
    MoE publication typeA1 Journal article-refereed

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